Let’s say you just decided whether to invest once a year, and your timeframe was for the next 10 years. What have been the 10 best, and worst years to invest since 1871? (10 year real returns, compounded).

Many of the best year starting points seem obvious in retrospect. 1948 and 1949 were good starting points, preceeding the Nifty Fifty mania, and of course 1918-1920 and the Roaring Twenties are on the list. 1988 and 1999 certainly would not be left out with the Internet bull market as well. Ditto for the bad years, they often fell at the end of massive bull runs. Notice anything about the best and worst times to invest? The average valuation (10 year CAPE) for the 10 best years was 10.92. The average valuation for the 10 worst years was 23.31, double that of the best starting points.